Water → 2-acetamido-N-(4-nitrophenyl)benzamide

HRID 1711339

Reaktionsgleichung

[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)C(O)=O)(=[O:3])[CH3:2].C1N=CN([C:19]([N:21]2C=N[CH:23]=[CH:22]2)=[O:20])C=1.[N+:26]([C:29]1[CH:35]=CC(N)=[CH:31][CH:30]=1)([O-:28])=[O:27].O>CN1CCCC1=O>[C:1]([NH:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:7][C:6]=1[C:19]([NH:21][C:22]1[CH:23]=[CH:35][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=1)=[O:20])(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 57.5 °C

Versuchsvorschrift

A mixture of 3-acetamidobenzoic acid (C1) (5.30 g, 29.58 mmol) and CDI (5.75 g, 35.50 mmol, 1.2 equivalent) in N-methylpyrrolidinone (20 mL) was heated at 55-60° C. for 2 h. 4-Nitroaniline (6.13 g, 44.37 mmol, 1.5 equivalent) was then added and the mixture was heated to 140° C. for 4 h, then poured into water (400 mL) and stirred for 18 h. The resulting precipitate was filtered and washed sequentially with water and CH2Cl2 and then crystallized from MeOH to give C2 (4.84 g; 55%) as a yellow solid; mp (MeOH) 259-261° C.; 1H NMR [(CD3)2SO] δ 10.80 (s, 1H, NH), 10.15 (s, 1 H, NH), 8.29 (m, 2H, H-3′ & H-5′), 8.12 (t, J=1.8 Hz, 1H, H-2), 7.84 (br dd, J=8.1, 1.2 Hz, 1H, H-6), 7.65 (td, J=7.8, 2.5 Hz, 1H, H-4), 7.48 (t, J=7.9 Hz, 1 H, H-5), 2.08 (s, 3H, COCH3); Anal. Calc. For C15H13N3O4: C, 60.2; H, 4.4, N, 14.0. found C, 60.4; H, 4.6; N, 14.1%.

Aufarbeitung

temperaturethe mixture was heated to 140° C. for 4 h
filtrationThe resulting precipitate was filtered
washwashed sequentially with water and CH2Cl2
customcrystallized from MeOH

Quellen und Nachweise

ORD-Eintrag: ord-037d80ef2bd5454e8a3eee08e52a1db4
Quelldatensatz: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07790746B2

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